


Measurements

by amadnesskinks



Category: Teen Wolf (TV)
Genre: Age Play, Always Female Stiles Stilinski, Anal Sex, Daddy Kink, F/M, Female Stiles Stilinski, Medical Kink, Size Kink
Language: English
Status: Completed
Published: 2014-10-09
Updated: 2014-10-09
Packaged: 2018-02-20 12:14:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,794
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2428322
Author URL: https://archiveofourown.org/users/amadnesskinks/pseuds/amadnesskinks
Summary: <blockquote class="userstuff">
              <p>Derek and Stiles make up after a fight.  Stiles just wants to be Derek's good little girl again, and Derek decides it's time to measure Stiles and see if she's big enough for her Daddy yet.</p>
            </blockquote>





	Measurements

**Author's Note:**

> Before we get started, some warnings:
> 
> This is my first fic on this account, also one of the kinkier things I've written since I left the SPN fandom, so I'm a little nervous. I've tried to do my best to polish, but if I missed anything let me know.
> 
> I was deliberately vague about Stiles' age in this. In my head she's over the age of consent, but this can definitely read as underage. If you're reading it as underage, it also comes off as extremely non-consensual, so please be aware of that aspect, too.
> 
> There's also unsafe/off-label uses of medical and office equipment. This is meant to be a fantasy, not a reflection of real life. Please don't try this at home.
> 
> Also, thank you to kinkyfics for the inspiration for this fic. (Links at the end.)
> 
> Onward!

“Are you going to be a good girl for your daddy, Stiles?” Derek asks, his voice a low rumble. Stiles shivers and nods, teeth sunk into her lip. “What do you say, sweetheart?” Derek coaxes.

“Yes, Daddy,” she whispers. “I’ll be good, Daddy.”

Derek smiles. “Good girl.” He comes closer, slides behind her and strokes his hands down, over her breasts until they cup her hips, his fingers tapping on her pubic bone. She’s so small next to him. Derek presses his mouth to her neck and breathes in the candy-perfume scent of her. “How good are you going to be for me, sweetheart?”

“So good, Daddy,” Stiles promises, twisting to look up at him with her big brown eyes. “I wanna be so good. I don’t like it when you’re mad at me.”

“Shh, sweetheart, it’s okay. I’m not mad anymore, I promise. And you remember why I was angry, don’t you?” Derek asks.

“Yes, Daddy,” she admits, pouting a little.

“Tell daddy why he was angry with you, sweetheart,” Derek prompts.

“Because I disobeyed,” Stiles says. “I said bad words and I didn’t answer when you called me on the phone. And then I said it didn’t matter and I was big enough not to need a daddy anymore.”

“But do you need a daddy still?” Derek asks, nuzzling behind her ear and pulling her closer against him.

“Yes, Daddy, I do. I need you,” she says earnestly. “I need you a lot and I didn’t really mean the things I said, I was just scared and sad because you had to go away.”

“That’s right,” Derek praises, kissing her temple. “I did have to go away. And I was mad at you because you said mean things, didn’t you?”

“Yes, Daddy,” Stiles says.

“I promise, baby girl, I’m not mad anymore. And I forgive you. And I’m sorry, too. I shouldn’t have told you I was leaving so last-minute, and I won’t do it again,” Derek says.

“Okay,” Stiles sniffs, sounding a little choked up.

“Are you ready to be my good little girl again, Stiles?” Derek asks.

“Yes, Daddy, I said so, didn’t I?” Stiles says, twitching against him like she wants to stomp her foot.

“You did,” Derek agrees. “And since it’s a special occasion, I thought I’d ask you what you wanted to do tonight.”

“We can do anything?” Stiles asks. “Anything I want?”

“You can ask me for anything,” Derek corrects. “But if I think you’re not ready, or you’re greedy, then I might say no.”

Stiles does pout now, her pretty pink lips stuck out as she frowns. “But I won’t be in trouble if I ask for it and you say no?” she asks finally.

“No, you won’t be in trouble. Was there something specific you wanted to ask for?” Derek asks.

“Yes, Daddy,” Stiles nods. “There’s something I want a lot but you say no all the time.”

Derek grins behind Stiles. He knows exactly what she’s talking about. “What do you want, Stiles? Won’t know if I’ll let you have it until you ask, pretty girl.”

She twists around in his arms and hooks her arms around his neck. “Daaaddy,” she wheedles, the toe of one shiny Mary Jane shoe dragging back and forth on the carpet as she presses up against him, trying to entice him into saying yes. “Daddy, what I really, really want is for you to put your cock in me, pleeeeease?”

“Hmm,” he hums, drawing it out a little to tease her. “Put my cock in you? I don’t know, baby. You know I don’t think you’re ready for that yet, sweetheart.”

“I am ready!” Stiles insists. “I can show you! I’ll show you how ready I am, I promise!”

“Well, I suppose I could measure you, see if maybe you’re ready to take something bigger than my fingers,” Derek agrees slowly, nodding a little. He’s been holding off on fucking her for months now, always fucking between her thighs, or letting her suck him off instead, but it is a special occasion, and she’s promised to be good.

“Yes!” Stiles agrees happily. “Yes, you should definitely measure me, Daddy, and see how big I am now.”

“All right. You go ahead and go get into bed and put your feet up like I showed you, and I’ll go get the measuring supplies.” Derek watches as she scurries off to the bedroom, already pulling her dress off so she can be ready for him to measure her when he gets there. He’s a little slower following her, stopping to get a few things from his office before he heads into his bedroom. She’s on her back on his bed, her ankles cuffed to his headboard so she’s spread open, her legs held wide, her pretty pink pussy and asshole on display for him. Derek ignores her for the moment, goes into his closet and takes a few things out of one of the toy boxes, then lays everything out on the bed.

“Come on, Daddy, hurry up!” she urges, wiggling a little. Her hands are free, but she keeps them at her sides, the way he taught her.

“All right, I’m here,” he assures her. “Which one first? Your little kitty, or your naughty place?”

Stiles makes a desperate noise when she sees what he’s holding. “Um! I don’t know, Daddy, I—my naughty place,” she squeaks.

Derek lubes up the anal speculum and slowly slides it inside Stiles’ asshole. “Okay?” he asks.

“Mm-hmm,” Stiles nods. “M’okay, Daddy,” she says, breathless.

“Okay. I’m gonna open you up now, sweetheart,” he says. He squeezes the handles together carefully, making sure she isn’t stretched too far, then waits while her rim flutters and twitches trying to get used to the stretch. “All right?” he asks.

“Daddy, Daddy, I don’t like it,” she whines.

“Why not, sweetheart?” he asks. “What don’t you like?”

“Makes me feel open and wrong,” she pants. “Like anybody could just—just touch me there and I couldn’t—couldn’t say stop.”

“I’m right here, baby, I’m not gonna let anybody touch you but me,” Derek promises.

Stiles chews on her lip, unconvinced.

“I have to open it more, sweetheart,” Derek warns, squeezing the handles again. “Gotta get you nice and loose so I can measure inside you, sweetheart. Don’t you want to know if you’re read to have my cock inside you?”

“Okay,” Stiles agrees, reluctant. Her cheeks are flushed pink and her fingers are clenching in the sheets. Derek squeezes again, opening her up even more. She squeals and tries to shift away from Derek, but with her legs up in the air and spread open she can’t get the leverage she needs. “Daddy, _please_ ,” she whines.

“Tell me what’s wrong, sweetheart,” he urges.

“So _big_ down there,” she whimpers. “Big and—and warm. Feels warm, like—I don’t know what it feels like, just—Daddy, please, I—I don’t want it,” she begs.

“We’re almost done, though, sweetheart,” he promises. “Just a little more and you’ll be ready to be measured.”

She digs her fingers into the sheets, her teeth into her lip, and shifts her hips desperately. “Okay,” she agrees finally. “Okay, you c-can.”

Derek uses his free hand to stroke her belly soothingly, his thumb dipping down and brushing her clit almost accidentally. Stiles jerks and pushes her hips up toward him. Derek squeezes again, then again, opening her a little faster now. He pauses again and Stiles whines helplessly. He keeps going then, until the handles are pressed together and she’s open as wide as the speculum will get her. “There you go, sweetheart, all done,” he praises. “You did so good.”

“Thank—thank you, Daddy,” she pants.

Derek picks up a ruler he’d grabbed from his office and slides it between the prongs of the speculum, sinks it down past the number eight and makes a show of marking off how deep it goes, then pulls it out and shows her. “See that? Almost nine inches, baby! That’s so good, that’s more than enough to take Daddy’s cock.”

She keeps chewing her lip, but smiles tentatively. “Yeah?” she asks.

“Definitely,” Derek nods. “You did so good. I’m going to take it out now, okay sweetheart? Just relax for me, baby girl.” He carefully slides the speculum out, letting her muscles push the prongs closed again as he removes it. “Now for the other one, sweetheart.”

He switches to the traditional speculum, lubes it up and slides it inside her vagina easily. Stiles jerks and cries out at the suddenness of it, but settles quickly. Derek’s deliberately rougher with her this time, opens the prongs a little too fast, and Stiles doesn’t have time to complain about it, just gasps and moans and squeaks as he opens her up and measures again.

“Oh, that’s too bad, sweetheart,” he says, showing her the second ruler. “Only four and a half inches in your little pussy.”

“Noooo, Daddy, _no_ , measure again, I want to be bigger than that,” Stiles protests, lifting her hips to try and catch him as he pulls the speculum back out and puts it aside. “Daaddyyyy,” she whines.

“Now hush sweetheart, you know the rules. If you’re not ready, then you’re not ready, and I’m not going to go too fast for your body to keep up and hurt you, sweetheart,” Derek admonishes.

“Yes, Daddy,” Stiles agrees petulantly.

“Do you need a spanking, sweetheart?” Derek asks, landing a warning swat on her cheek even as she shakes her head.

“No, Daddy, I don’t need one,” she insists.

“Hmm,” Derek frowns, slapping her butt a few more times before stopping. “Well, all right.”

“Daddy,” Stiles hints, trying to nudge him with a knee but not quite able to reach him. “Daddy, you said.”

“What did I say?” Derek asks, feigning ignorance over what she wants.

“You said if I was big enough you’d put your cock in me,” she says.

“I did say that,” Derek nods.

“And you said my naughty place was big enough,” Stiles continues, “and you said I could ask for whatever I wanted tonight because it was special, and I asked for you to put your cock in me. Please Daddy?”

Derek purses his lips and pretends to resist for a moment before he leans over Stiles and presses a kiss to her pretty mouth. “All right, baby girl. Daddy will put his cock in you. But you know I have to put it in your naughty place, right? You didn’t like it when I was measuring you before. Are you sure you really want it?”

“Yes, Daddy, I’m sure,” Stiles nods. “I want to be good for you! I want to show you how big I am.”

“Well, all right, then,” Derek agrees. He picks up the lube and slicks his cock, then pushes more lube into her asshole. “We want to make sure you’re nice and slippery for Daddy, baby. Don’t want to hurt you.”

“It’s okay, Daddy,” she says proudly. “I wouldn’t mind if it hurt a little.”

“No? You mind your spankings,” he reminds her. “You mind when I pinch your little nipples and put them in clamps.”

“That’s because those things actually _hurt_ ,” she points out. “You spank me really hard, Daddy. And the clamps are metal and ouchy. And you pull on them and it’s not nice.”

“I think it’s nice,” Derek protests. “And last time your little pussy got all sloppy and wet for me, remember?”

“Yes, but it still hurt,” Stiles sniffs.

Derek stops fingering lube into her ass and wipes his hands clean. “Ready, sweetheart?” he asks.

“Yes,” Stiles nods. “Daddy? Will you take off your shirt and pants? Please?”

“I could do that, sweetheart. Any reason why?”

“I like to feel your skin on mine,” she says, and grins up at him when he strips off his shirt. “Thank you, Daddy!”

“You’re welcome, sweetheart,” Derek croons, stroking his hand down between her breasts and over her belly. Carefully, he slots the head of his cock into her ass, petting the stretched muscle of her rim as he does. She shivers, fingers clenching again in the sheets. “Okay?”

“Yes, Daddy,” Stiles nods.

Derek feeds more of his dick into her hole, watching as she takes him easily. She doesn’t make a sound while he pushes inside her, and he’s a little worried he’s pushed too much, tried to have her take too much at once, but when he bottoms out she shudders and sighs, her face going slack with pleasure. “How do you feel, baby girl?” Derek asks, petting her belly again.

“Mm, s’full, Daddy,” Stiles mumbles, blinking and trying to shift her hips. “You’re so big. S’a lot.”

“It doesn’t hurt, though?” Derek presses.

“No, Daddy,” Stiles shakes her head. “Feels good. Full is good.”

“Okay,” Derek smiles. “I’m going to start moving now, sweetheart.”

“Yes, Daddy,” Stiles sighs happily, wiggling as much as she can manage.

Derek starts fucking her slowly, and she opens around him so easily that he speeds up almost without meaning to. She whines a little as he fucks her steadily, his hands on her stomach, her breasts.

“Daddy, please—“ she gasps.

“What is it, baby?” he encourages her. “You can ask.”

“Please, will you touch my pretty place?” she asks, fingers twitching in the sheets.

Derek doesn’t answer right away, just braces himself with one arm and leans back so he can see her perfect, exposed cunt. “So greedy, sweetheart,” he says softly. “Don’t know if I should indulge you.”

“Oh, please Daddy,” she begs, “ _please_?”

“Well,” Derek hesitates, then relents. “All right, baby. You did ask me nicely, after all.”

“Thank you, Daddy,” Stiles gasps out, even as Derek dips two fingers inside her slick, pink pussy and swirls them around. “Oh—oh fuck, Daddy, so good.”

“That’s my girl,” Derek praises, thumbing her clit almost absently as he finger fucks her. He keeps his fingers shallow at first, then starts sliding deeper and crooking them up. She keens when he hits the right place, just on the edge, and Derek does it again, then goes back to rubbing her clit with his fingers.

Stiles pants helplessly for a few minutes, lets him finger her and rub against her clit while he fucks her, but his girl has never been passive, and before too long she’s whining and begging and canting her hips toward him for a better angle.

“Oh, sweetheart, look at you,” Derek purrs. “So eager. Maybe if you’re very good and let me put my fingers in you more often, then next time we measure you, you’ll be big enough for my cock in your pussy, baby. Would you like that? I bet you would.” Stiles whines again and starts to lift her hands from the sheets, but catches herself. “You’re being so good for me, sweetheart. So perfect. You want to be extra good for Daddy, don’t you baby?”

“Yes, Daddy,” Stiles nods. “Wanna be so good for you. Don’t want you to be mad anymore, don’t want you to ever be mad. Just wanna be your good girl,” she moans and arches her back as she finishes, and Derek leans down and licks one pink nipple.

“I know you do, baby. You want to be my very best girl, don’t you?” Stiles nods, and Derek kisses the pretty pink bud, then slides his fingers back inside Stiles. “You can come whenever you want, sweetheart,” he says, and his hips snap forward as his fingers sink deep, and his thumb slides just perfectly over her clit. Stiles’ whole body convulses, comes up off the bed, and Derek watches as she comes apart around him, her stretched-out anal muscles doing their best to contract around him.

“Daddy, _Daddy_ ,” she squeals as she comes. “Oh, fuck, Daddy—“

Derek fucks her through her orgasm, and when she doesn’t signal him to stop or slow down after she’s come, he speeds up and chases his own orgasm. It doesn’t take him long, and he comes inside her with a grunt.

“Daddy,” Stiles whispers happily, rubbing one hand through his hair.

“Yeah, baby,” Derek mumbles. He pushes himself up and helps her unhook her legs from the headboard, then kisses her forehead and rolls out of bed so he can clean up the toys they used. He dumps the dirty toys in the bathtub and comes back to Stiles with a warm, wet washcloth. She clings to his neck as he wipes them both down, and when he’s done he lets himself be pulled down for kisses.

“You’re the best, Der,” she slurs in his ear. “Love you.”

He doesn’t say it back, but he doesn’t need to. She already knows.

**Author's Note:**

> Inspired by this gif/prompt/idea from Kinkyfics--http://kinkyfics.tumblr.com/post/93938043253/submitted-by-wetprinc3ss-all-i-see-is-a-young


End file.
